Ethyl Acetate → HCID 9798366, compound

HRID 2081592Notes

Reaction equation

HRID 2081592 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][CH2:22][N:23]1[C:28]([CH3:30])([CH3:29])[CH2:27][CH2:26][CH2:25][C:24]1([CH3:32])[CH3:31].C(OCC)(=O)C>CN(C)C=O.O>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([S:1][CH2:21][CH2:22][N:23]3[C:28]([CH3:30])([CH3:29])[CH2:27][CH2:26][CH2:25][C:24]3([CH3:31])[CH3:32])[NH:3][C:4]=2[CH:10]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 219144831-(2-Chloroethyl)-2,2,6,6-tetramethylpiperidine--hydrogen chloride (1/1)HCID 178488032HCID 178488032, compound

Product 1

HCID 9798366HCID 9798366, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 15 ml of N,N-dimethylformamide was dissolved 810 mg of 2-mercapto-5-methoxybenzimidazole, and 933 mg of potassium carbonate and 1.62 g of 1-(2-chloroethyl)-2,2,6,6-tetramethylpiperidine hydrochloride were added to the solution, followed by stirring at 65° to 70° C. for 4.5 hours. After completion of the reaction, 200 ml of ethyl acetate and 70 ml of water were added to the reaction mixture, and the thus extracted ethyl acetate layer was washed successively with a diluted sodium hydrogencarbonate aqueous solution and a diluted sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The extracting solution was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=50:1 to 25:1 by volume) to obtain 1.25 g (80%) of the titled compound.

Workup

  1. additionwere added to the solution
  2. additionwere added to the reaction mixture
  3. washthe thus extracted ethyl acetate layer was washed successively with a diluted sodium hydrogencarbonate aqueous solution
  4. dry with materiala diluted sodium chloride aqueous solution and dried over anhydrous magnesium sulfate
  5. customThe extracting solution was removed by distillation under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol=50:1 to 25:1 by volume)

Sources & evidence

ORD record
ord-ce16192026a447d78cac11b76699eb2a
Source dataset
uspto-grants-1993_02
Patent number
US05185347

Reaction notes

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